The JCR: A Massey Podcast

The JCR: A Massey Podcast


Surprise, You’re a Startup Founder! A Conversation with Philip Playfair

October 03, 2025

What do innovators and startup founders have in common? Surprises! Philip Playfair studied history and planned on a career in public service. Instead, he became a startup founder, building strong teams and solving real customer needs with technology. A self-described accidental serial entrepreneur, Playfair’s path shows how unexpected turns, and even being unprepared (!) can lead to bold, brilliant moves into entrepreneurship. In this episode, Playfair joins Silicon Valley native and Massey Junior Fellow Anne-Marie Fowler to reflect on the surprises that catch founders off guard, and the opportunities that come from embracing the unexpected.

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